Navegando por Assunto "Flavonóides"

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Arrabidaea chica (HBK) Verlot: phytochemical approach, antifungal and trypanocidal activities
(2008-12) BARBOSA, Wagner Luiz Ramos; PINTO, Lucianna do Nascimento; QUIGNARD, Etienne Louis Jacques; VIEIRA, José Maria dos Santos; SILVA JÚNIOR, José Otávio Carréra; ALBUQUERQUE, Sérgio de
Arrabidaea chica (HBK.) Verlot (Bignoniaceae) vernacular name "Pariri", is a climbing shrub, widespread from South Mexico to Guyana and central Brazil and is traditionally indicated to treat symptoms of inflammations and skin affections. Its ethanol extract was chemically investigated and tested against yeasts and dermatophytic fungi. The trypanocidal activity of the same extract was also evaluated. This work reports the isolation of three flavonoids, the total growth inhibition of Trichophyton mentagrophytes and a significant trypanocidal effect of the ethanol extract and its fractions. No relevant acute toxicity was detected even at a dose of 1000 mg/kg
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Atividade antiproliferativa e antineoplásica de flavonóides da espécie Brosimum acutifolium em modelo de glioblastoma in vitro
(Universidade Federal do Pará, 2013-05-24) MAUÉS, Luis Antônio Loureiro; NASCIMENTO, José Luiz Martins do; http://lattes.cnpq.br/7216249286784978
Among the tumors that affect the nervous system, glioblastoma multiforme (GBM) is notable by its high degree of aggressiveness and poor prognosis, with an average survival of 15 months from diagnosis. The present study aimed to investigate the antiproliferative and antineoplastic activity of four flavonoids isolated from species Brosimum acutifolium (Huber). two flavans: 4'-hydroxy-7,8-(2",2"-dimethylpyran)-flavan (BAS-1) and 7,4'-dihydroxy-8-(3,3-dimethylallyl)-flavan (BAS-4), and two chalcones: 4,2'-dihydroxy-3',4'-(2",2"-dimetilpirano)-chalcone (BAS-6) and 4,2',4'-trihydroxy-3'-(3,3-dimethylallyl)-chalcone (BAS-7), tested on rat C6 glioblastoma in vitro. Our results showed good cytotoxic activity for flavans (BAS-1, -4) and the chalcone BAS-7, with IC50 less than 100 μM in the MTT viability test, since the chalcone BAS-6, showed no cytotoxicity at the concentrations tested. These flavonoids showed less cytotoxity for non-neoplastic cell (glia), with higher degree of security for the BAS and BAS-4-7, once showed lower cytotoxic effect on non-neoplastic cell, and less hemolytic. Analysis of cell migration showed that treatment with BAS-1; -4 and -7 at low concentrations was effective in promoting the inhibition of cell migration. These three flavonoids were also very promising in inhibiting colony formation and growth, and promote cell cycle arrest with a substantial increase in population SubG0 for treatment with BAS-1 and -4 with 100 μM. The flavans BAS-1 and -4 also showed increased ability to promote losing in the integrity of the mitochondrial membrane potential (ΔΨm) and increased for staining with Annexin V, indicating that these drugs cause death by apoptosis. However the analysis by electron microscopy showed markedly the presence of autophagic vacuoles in the treatment with BAS-4 suggesting that the process of cell death occurs by apoptosis as well as autophagy. Based on these results it can be concluded that the flavonoids BAS-1, -4, and -7 have potential as an anticancer agent in the therapy of GBM and BAS-4 is the most promising of all.
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Biflavones and triterpenoids isolated from Ouratea castaneifolia (DC.) Engl., Ochnaceae
(2009-12) NASCIMENTO, Luís Adriano Santos do; GUILHON, Giselle Maria Skelding Pinheiro; ARRUDA, Mara Silvia Pinheiro; SANTOS, Lourivaldo da Silva; ARRUDA, Alberto Cardoso; MÜLLER, Adolfo Henrique; SILVA, Milton Nascimento da; RODRIGUES, Silvane Tavares; CARVALHO, Mário Geraldo de
This paper presents the chemical investigation of the leaves and stems of Ouratea castaneifolia (DC.) Engl.. There are no chemical or pharmacological studies with this species. Classic phytochemical investigation of the organic extracts together with high pressure liquid chromatography (HPLC) procedures lead to the identification of seventeen metabolites: seven triterpenes (friedelin, 3β-friedelinol, α-amyrin, β-amyrin, lupeol, germanicol and taraxerol), four steroids (sitosterol, stigmasterol and the glycosides sitosteryl 3-O-β-D-glucopyranoside and stigmasteryl 3-O-β-D-glucopyranoside), one isoflavone (5,7,4’-trimethoxyisoflavone), one flavone (5,4’-dihydroxy-7,3’,5’-trimethoxyflavone) and four biflavones (amenthoflavone, 7,7”- O-dimethylamenthoflavone, heveaflavone and tetramethylamenthoflavone). The structures of the compounds were established by the analysis of 1H, 13C NMR spectra including bidimensional techniques. The classes of the identified metabolites are in agreement with previous studies of the Ouratea genus.
Acesso aberto (Open Access)
Caracterização do mecanismo de ação antiinflamatória do flavonóide BAS1 isolado da planta Brosimum acutifolium
(Universidade Federal do Pará, 2011-08-02) MORAES, Waldiney Pires; SILVA, Anderson Manoel Herculano Oliveira da; DINIZ, Domingos Luiz Wanderley Picanço; http://lattes.cnpq.br/9601463988942971
Inflammation is the body's response to injury and danger. Even though it’s a body defensive mechanism, this response’s intensity and/ or persistency might be harmful for an individual. In such context, natural products are important sources of biologically active molecules, and they’re considered promising resources for the discovering of new drugs. Based on ethno pharmacological studies, BAS1 flavonoid (4'-hydroxy, 7, 8 - (2'', 2''-dimethyl-pyran)-flavan), which hasn’t been described by literature yet, was isolated from the Brosimum acutifolium plant, popularly known as "mururé da terra-firme." Facing this, the present study aimed at characterizing the anti-inflammatory mechanism of action of BAS1 flavonoid in stimulated murine macrophages. Macrophages were activated with LPS and IFN-γ, cell viability was evaluated by the MTT, levels of inflammatory mediators were determined by ELISA (TNF-α, PGE2, IL-10) through Griess reaction (NO) and protein expression by Western blotting. The results demonstrate that BAS1 only has cyclotoxic effects at high concentrations (100 μM) inhibited NO production (95%), negatively regulated the expression of NOS-2, reduced the TNF-α production (39%) and PGE2 (57%), but didn’t with IL-10 in activated macrophages. Thus, demonstrating the pharmacological effect of BAS1 flavonoid, as well as supporting the usage of the Brosimum acutifolium plant as an anti-inflammatory in our region was an important contribution from this study. Furthermore, the production of this plant’s extract could provide the local population with an effective and affordable anti-inflammatory. The present work may also contribute to the establishment of a new classification of anti-inflammatory agents, based on natural flavonoids, such as BAS1.
Acesso aberto (Open Access)
Dihydroflavonols from the leaves of Derris urucu (Leguminosae): structural elucidation and DPPH radical-scavenging activity
(2009) LÔBO, Lívia Trindade; SILVA, Geilson Alcantara da; FERREIRA, Malisson; SILVA, Milton Nascimento da; SANTOS, Alberdan Silva; ARRUDA, Alberto Cardoso; GUILHON, Giselle Maria Skelding Pinheiro; SANTOS, Lourivaldo da Silva; BORGES, Rosivaldo dos Santos; ARRUDA, Mara Silvia Pinheiro
Derris urucu is an Amazonian plant with insecticide and ichthyotoxic properties. Studies with this species show the presence of flavonoids, mainly rotenoids, as well as stilbenes. The ethanol extract of the leaves of Derris urucu (Leguminosae) afforded three new dihydroflavonols named urucuol A (1), B (2) and C (3), and the dihydroflavonol isotirumalin (4). Their structures were elucidated by extensive analysis of 1D and 2D NMR, UV and IR spectra and MS data and comparison with literature data. The isolated compounds (1-4) were evaluated for DPPH• radical scavenging activity and showed a relatively lower antioxidant ability compared to the commercial antioxidant trans-resveratrol.
Acesso aberto (Open Access)
Flavones from the Leaves of Ficus gomelleira
(2001-08) AMARAL, Daniel Ferreira; ARRUDA, Mara Silvia Pinheiro; ARRUDA, Alberto Cardoso; MÜLLER, Adolfo Henrique; PANTOJA, Luna Luana de Jesus; LIMA, Tania Maria da Silva
Two new flavones, 5 -hydroxy -7,5' -dimethoxy -3',4' -methylenedioxyflavone and 5 -hydroxy -7,3',5' -trimethoxy -4' -(3,3 -dimethylallyloxy) flavone, as well as three known flavones: 5,6,7,3',4',5' -hexamethoxyflavone, 5 -hydroxy -8,3',4' -trimethoxy -2'',2'' -dimethylpyrano (5",6":6,7) -flavone and 5 -hydroxy -8,3',4',5' -tetramethoxy -2'',2'' -dimethylpyrano (5",6":6,7) -flavone were isolated from the leaves of Ficus gomelleira. Their structures were elucidated by spectroscopic methods and comparison with literature data.
Acesso aberto (Open Access)
Flavonoids from leaves of Derris urucu: assessment of potential effects on seed germination and development of weeds
(2013-09) SILVA, Ewerton Afonso Silva da; LÔBO, Lívia Trindade; SILVA, Geilson Alcantara da; SOUZA FILHO, Antonio Pedro da Silva; SILVA, Milton Nascimento da; ARRUDA, Alberto Cardoso; GUILHON, Giselle Maria Skelding Pinheiro; SANTOS, Lourivaldo da Silva; ARRUDA, Mara Silvia Pinheiro
In some previous studies, we described the isolation of nine compounds from leaves of Derris urucu, a species found widely in the Amazon rainforest, identified as five stilbenes and four dihydroflavonols. In this work, three of these dihydroflavonols [urucuol A (1), urucuol B (2) and isotirumalin (3)] were evaluated to identify their potential as allelochemicals, and we are also reporting the isolation and structural determination of a new flavonoid [5,3′-dihydroxy-4′-methoxy-(7,6:5″,6″)-2″,2″-dimethylpyranoflavanone (4)]. We investigated the effects of the dihydroflavonols 1-3 on seed germination and radicle and hypocotyl growth of the weed Mimosa pudica, using solutions at 150 mg.L–1. Urucuol B, alone, was the substance with the greatest potential to inhibit seed germination (26%), while isotirumalin showed greater ability to reduce the development of the hypocotyl (25%), but none of the three substances showed the potential to inhibit radicle. When combined in pairs, the substances showed synergism for the development of root and hypocotyl and effects on seed germination that could be attributed to antagonism. When tested separately, the trend has become more intense effects on seed germination, while for the substances tested in pairs, the intensity of the effect was greater on development of weed.
Acesso aberto (Open Access)
Flavonoids from the leaves of Deguelia utilis (Leguminosae): structural elucidation and neuroprotective properties
(2012-10) OLIVEIRA, Dalglish Gomes de; ALMEIDA, Cecília M. C. de; SILVA, Consuelo Yumiko Yoshioka e; ARRUDA, Mara Silvia Pinheiro; ARRUDA, Alberto Cardoso; LOPES, Dielly Catrina Favacho; YAMADA, Elizabeth Sumi; COSTA, Edmar Tavares da; MARTINS FILHO, Arnaldo Jorge; SILVA, Milton Nascimento da
Five new flavonoids, 5,3'-dihydroxy-4'-methoxy-2'',2''-dimethylchromene-(5'',6'':6,7)dihydroflavonol (1), 5,3'-dihydroxy-7,4'-dimethoxy-6,8-dimethylallyl-dihydroflavonol (2), 5,3'-dihydroxy-4'-methoxy-8-allyl-2'',2''-dimethylchromene-(5'',6'':6,7) flavanone (3), 5,3'-dihydroxy-7,4'-dimethoxy-6,8-dimethylallyl-flavanone (4), 3,5,3'-trihydroxy-7,4'-dimethoxy6,8-dimethylallyl-flavanol (5), together with the stilbenes 4-methoxylonchocarpene (6) and lonchocarpene (7) were isolated from the leaves of Deguelia utilis. Their chemical structures were established on the basis of NMR (nuclear magnetic resonance) spectral data and HRESITOF-MS (electrospray ionization-high resolution time-of-flight mass spectrometry). Also, in order to investigate potential cytoprotective effects of these flavonoids, we used a fraction eluted with hexane:EtOAc containing all seven flavonoids, in an in vitro model of neurodegeneration, using hippocampal primary cultures from neonatal (PND2-P3) rats exposed to rotenone, a mitochondrial complex I inhibitor. There was a significant reduction in cell viability (19.4 ± 1.6%) when the cultures were exposed to 30 nmol L-1 rotenone for 72 h. Concomitant exposure of the cultures to the FR3 (5 µg mL-1) and 30 nmol L-1 rotenone resulted in values of cell viability similar to control groups (99.6 ± 4.8%), strongly suggesting a cytoprotective effect for this flavonoid-rich fraction.
Acesso aberto (Open Access)
Isolamento e quantificação de flavonóides e abordagem das atividades antioxidante e antimicrobiana de Jatropha gossypiifolia L.
(Universidade Federal do Pará, 2008-12-30) VEIGA, Andrex Augusto Silva da; BARBOSA, Wagner Luiz Ramos; http://lattes.cnpq.br/1372405563294070
Jatropha gossypiifolia L (Euphobeaceae), known in Pará as “Pião roxo” is used for treatment of hemorroids, burns, stomach pains among other diseases, the importance of this plant to this region has led to its research in order to improve its phytotherapeutic development. During the analysis, the chromatographic profiles of its Crude Ethanolic Extract (CEE)was determined using Thin Layer chromatography (TLC) and High Performance Liquid Chromatography (HPLC) methods. The total and isolated flavonoids quantities were determined. Antimicrobial activity essays of the crude ethanolic extract were also conducted and the fractions obtained (hexanic, chloroform, ethyl acetate and residual fractions). The antioxidant activities of the extract and the fractions were also characterized. The plant materials were collected from EMBRAPA medicinal plants garden in the east Amazon and then extracted through percolation to obtain crude ethanolic extract. The dry extract was obtained using low pressure rotative evaporator followed by liquid-liquid partition with hexane, chloroform and ethyl acetate successively. The fractions obtained were also concentrated at low pressure, The ethyl acetate fractions were re-fractioned, giving rise to acetone fraction (ActF-II), a new ethyl acetate (AF-II), methanolic fraction (MF-II) and a solid residue (SR-II). ActF-II was submitted to liquid chromatography at average pressure, resulting in sub-fractions like Fr ActS-II and Fr ActS3-II called Jg1 and Jg2, respectively. Chemical prospection of the Extract and the metabolite fractions were conducted in triplicates, leading to the observation of the presence of the following polyphenols: Catechines, Tannins and flavonoids. The analysis by thin Layer Chromatography (TLC) was conducted using eluent of ethyl acetate/formic acid/glacial acetic acid/water at (100:11:11:26) on a normal phase silica gel, showing the retention factors in the following zones:0.65, 0.72, and 0.77 in reaction to Fecl3 solution . The HPLC chromatogram of ethanolic crude extract presented three significant peaks with average values of RT: 13.2 min, 15.02 min, and 16.00 min whose spectra are characteristics of flavonoids. On calculating the flavonoid quantity using the average absorbance reading (A=0.874), 2.02% flavonoid was found. The concentrations for each isolated substances was 340ug for Jg1 and 406 ug for Jg2 per milliliter of extract solution. Regarding the biological activity tested AF-1 and Fr-1 inhibited growths of S. aureus and C.albicans and also manifested a great antioxidant potential. These results provide adequate polyphenol parameters for quality control serving as chemical markers and their possible quantities.
Acesso aberto (Open Access)
A New Prenylisoflavone from the Antifungal Extract of Leaves of Vatairea guianensis Aubl.
(Universidade Federal do Pará, 2017-06) SOUZA, Ronilson Freitas de; SILVA, Geilson Alcantara da; ARRUDA, Alberto Cardoso; SILVA, Milton Nascimento da; SANTOS, Alberdan Silva; GRISÓLIA, Daniella Paternostro de Araújo; SILVA, Moisés Batista da; ARRUDA, Mara Silvia Pinheiro
A new compound, 5,7,3'-trihydroxy-4'-methoxy-8-prenylisoflavone, was isolated from the leaves of Vatairea guianensis Aubl. (Fabaceae), together with two known isoflavones lupiwighteone and 5,7,4'-trihydroxy-3'-methoxy-8-prenylisoflavone. All isolated compounds were characterized based on infrared (IR), UV, 1H and 13C nuclear magnetic resonance (NMR), including 2D NMR analyses and high resolution mass spectrometry. The ethanolic extract from V. guianensis leaves displayed activity against Candida dubliniensis, C. albicans and C. krusei. However, the EtOAc fraction from that extract exhibited more significant activity than the ethanolic extract, showing antifungal activity for all fungi species investigated. The major compound 5,7,3'-trihydroxy-4'-methoxy-8-prenylisoflavone isolated from that EtOAc fraction was also active against C. parapsilosis and C. dubliniensis.